Asymmetric epoxidation catalyzed by N-aryl-substituted oxazolidinone-containing ketones: Further evidence for electronic effects

Organic Letters

Volumn 5, Issue 3, 2003, Pages 293-296

  Shu, Lianhe ^a   Wang, Pingzhen ^a   Gan, Yonghong ^a   Shi, Yian ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLCYCLOHEXANE; ALKENE; BETA METHYLSTYRENE; CYCLOHEXENE DERIVATIVE; KETONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; STYRENE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG; KETONE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; EPOXIDATION; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; OXIDATION REDUCTION REACTION;

CATALYSIS; ELECTRONS; KETONES; MOLECULAR STRUCTURE; OXAZOLIDINONES; OXIDATION-REDUCTION;

EID: 0037841906     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020229e     Document Type: Article

References (50)

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17. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
18. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
19. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
20. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
21. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
22. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
23. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
24. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
25. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
26. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
27. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
28. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
29. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
30. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
31. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
32. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
33. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
34. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
35. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
36. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
37. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
38. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
39. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.;
40. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
41. For leading references on asymmetric epoxidation mediated in situ by chiral ketones, see: (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831. (c) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; DePue, J. S.; Wilde, R. G. J. Org. Chem. 1995, 60, 1391. (d) Brown, D. S.; Marples, B. A.; Smith, P.; Walton, L Tetrahedron 1995, 51, 3587. (e) Yang, D.; Yip, Y. C.; Tang, M. W.; Wong, M. K.; Zheng, J. H.; Cheung, K. K. J. Am. Chem. Soc. 1996, 118, 491. (f) Yang, D.; Wang, X.-C.; Wong, M.-K.; Yip, Y.-C.; Tang, M.-W. J. Am. Chem. Soc. 1996, 118, 11311. (g) Song, C. E.; Kim, Y. H.; Lee, K. C.; Lee, S. G.; Jin, B. W. Tetrahedron: Asymmetry 1997, 8, 2921. (h) Adam, W.; Zhao, C.-G. Tetrahedron: Asymmetry 1997, 8, 3995. (i) Denmark, S. E.; Wu, Z.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288. (j) Wang, Z.-X.; Shi, Y. J. Org. Chem. 1997, 62, 8622. (k) Adam, W.; Fell, R. T.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1998, 9, 397. (l) Armstrong, A.; Hayter, B. R. Chem. Commun. 1998, 621. (m) Yang, D.; Wong, M.-K.; Yip, Y.-C.; Wang, X.-C.; Tang, M.-W.; Zheng, J.-H.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 5943. (n) Yang, D.; Yip, Y.-C.; Chen, J.; Cheung, K.-K. J. Am. Chem. Soc. 1998, 120, 7659. (o) Adam, W.; Saha-Moller, C. R.; Zhao, C.-G. Tetrahedron: Asymmetry 1999, 10, 2749. (p) Carnell, A. J.; Johnstone, R. A. W.; Parsy, C. C.; Sanderson, W. R. Tetrahedron Lett. 1999, 40, 8029. (q) Armstrong, A.; Hayter, B. R. Tetrahedron 1999, 55, 11119. (r) Armstrong, A.; Hayter, B. R.; Moss, W. O.; Reeves, J. R.; Wailes, J. S. Tetrahedron: Asymmetry 2000, 11, 2057. (s) Solladie-Cavallo, A.; Bouerat, L. Org. Lett. 2000, 2, 3531. (t) Bortolini, O.; Fogagnolo, M.; Fantin, G.; Maietti, S.; Medici, A. Tetrahedron: Asymmetry 2001, 12, 1113. (u) Seki, M.; Furutani, T.; Imashiro, R.; Kuroda, T.; Yamanaka, T.; Harada, N.; Arakawa, H.; Kusama, M.; Hashiyama, T. Tetrahedron Lett. 2001, 42, 8201. (v) Armstrong, A.; Moss, W. O.; Reeves, J. R. Tetrahedron: Asymmetry 2001, 12, 2779. (w) Matsumoto, K.; Tomioka, K. Tetrahedron Lett. 2002, 43, 631. (x) Stearman, C. J.; Behar, V. Tetrahedron Lett. 2002, 43, 1943. (y) Denmark, S. E. ; Matsuhashi, H. J. Org. Chem. 2002, 67, 3479. (z) Shing, T. K. M.; Leung, G. Y. C. Tetrahedron 2002, 58, 7545.
42. For examples of asymmetric epoxidation mediated in situ by fructose-derived ketones, see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
43. For examples of asymmetric epoxidation mediated in situ by fructose-derived ketones, see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
44. For examples of asymmetric epoxidation mediated in situ by fructose-derived ketones, see: (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224. (c) Shu, L.; Shi, Y. Tetrahedron 2001, 57, 5213.
45. (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551
46. (b) Tian, H.; She, X.; Xu, J.; Shi, Y. Org. Lett. 2001, 3, 1929.
47. (c) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435.
48. Other nonbonding interactions such as hydrophobic interactions could also contribute to the observed enantioselectivity.
49. For an observation of electronic interaction in ketone-catalyzed asymmetric epoxidation, see ref 6n.
50. Hodge, J. E.; Fisher, B. E. Methods Carbohydr. Chem. 1963, 2, 99.